On a wild day of free-agent signings and trades, the best course of action was to play it safe. There were deals to be had, certainly, but a lot of general managers are going to look back at July 5, 2013, with regret and despair. After all that money was thrown around, the truth remains that only 16 out of the 30 teams make the playoffs each year, and only one wins the Stanley Cup. That doesn’t mean that every check written was a waste, but some were definitely worse than others.

Here are the teams who have the most reason to worry that they have gone wrong, the biggest losers of Friday’s action...

A staggering seven-year, $36.75 million contract for David Clarkson, and $21 million over five years for Tyler Bozak. Factor in the restricted free agents that the Maple Leafs still have to re-sign, and they are going to be right at the salary cap with a roster that still lacks a bonafide No. 1 center, features a staggering lack of defensive depth, and which figures to employ two facepunchers at a time in Frazer McLaren, who re-signed Friday, and Colton Orr.

Of course, Bozak is supposed to be that No. 1 center, but proof that he actually is—rather than just someone who happens to take faceoffs with Phil Kessel on the ice, and happens to be good pals with Kessel—remains elusive. Players who have never had more than 47 points in a season do not tend to be candidates for five-year deals at more than $4 million per season.

Then there is Clarkson, of whom general manager Dave Nonis said, “I believe he has a lot of good years left in him.” He’d better, having just signed for seven years.

Honestly, though, what are the odds of that? Clarkson is 29 and plays a physical game that takes a toll on the body. He has scored 97 goals with 770 penalty minutes in his career. The other active forwards who scored between 50 and 100 goals and had more than 700 penalty minutes through their age-28 seasons are Chris Neil and Steve Ott. Neil, the player the Maple Leafs are probably hoping Clarkson winds up being, has never made more than $2.1 million in a season. Ott will make $3.2 million this season and remains best known for chirping Claude Giroux on "24/7." If Sean Avery were still playing, he’d be on this list, too, but Sean Avery is not still playing.

Someone was always going to overpay for Bozak on Friday. Someone was always going to overpay for Clarkson on Friday. Turns out, the Leafs were the someone in both cases. Meanwhile, no replacement is at hand for Mikhail Grabovski or Clarke MacArthur.

Signing Jonathan Bernier and having another team offer-sheet him is nice, but the Leafs sill are left with a goaltending controversy of their own making as the new man battles incumbent James Reimer for the No. 1 job. Bernier, acquired last month via trade with the Los Angeles Kings, counts $2.9 million against the cap for the next two years.

Buying out Vincent Lecavalier provided the necessary salary cap room to sign Valtteri Filppula to a five-year, $25 million contract. Yes, that Valtteri Filppula. Yes, the 29-year-old center who had a very nice 2011-12 season with 66 points, but otherwise has had exactly one 40-point campaign in his NHL career.

The Lightning did nothing to address the fact that last season’s team allowed 3.06 goals per game, fifth-worst in the league. Instead, Tampa Bay spent the bulk of its buyout savings on one player who is four years younger and $2.7 million per season cheaper than Lecavalier was, but also has nowhere near Lecavalier’s profile.

“We feel (Filppula) is an outstanding, all-around centerman who brings a winning pedigree to our organization,” said general manager Steve Yzerman, who used to play for the Detroit Red Wings, where Filppula got his winning pedigree—in fact, they were both on the Red Wings in 2005-06, Yzerman’s final season. “He fills a much-needed position for us at center and his skill, work ethic and character will make him a great addition to our team.”

Center was a much-needed position because the Lightning bought out Lecavalier, who also had skill, work ethic and character.

Signing first-round pick Jonathan Drouin was a nice consolation for a disappointing trip to the free agent market, but he also does not do anything about the fact that Tampa Bay gives up far too many goals. That may have been something worth addressing, and it’s not like that is a new problem for a team whose defense was dead last in the NHL two seasons ago. Maybe Ben Bishop will prove to be a great goaltender who needs no more defensive help than he is already getting.

Another case of a curious buyout, as Tom Gilbert was sent packing so that Minnesota could afford to add someone else’s bought-out defenseman, the less-good Keith Ballard, formerly of the Vancouver Canucks. The real coup, though, was signing Matt Cooke to a three-year, $7.5 million contact to do whatever it is that he does.

Changed man though Cooke may be from the player who was just about set to get thrown out of the league for hitting people in the head, he has not exactly become some kind of dynamic player. He’s 34 years old, and while he is a rough customer, Minnesota already pays Zenon Konopka and Mike Rupp less money combined than Cooke’s $2.5 million per year for rough customer service. For a team with almost no cap room, an antagonist of Cooke’s level is a luxury that must be done without, which is precisely why the cap-strapped Pittsburgh Penguins let him go.

Meanwhile, the Wild had to let a solid contributor get away in center Matt Cullen, who signed with the Conference III-rival Predators, and traded Devin Setoguchi to the Jets for a second-round draft pick. Cullen’s loss will be tougher for the Wild to take.

“He’s been a good teammate, he’s a hard-working guy, he’s a good hockey player and he’s a pro,” GM Chuck Fletcher told Michael Russo of the Minneapolis Star-Tribune. “It’s hard to replace guys like that.”

Dishonorable mentions

Ilya Bryzgalov and Tim Thomas saw a starter’s job come off the board when Evgeni Nabokov re-signed with the Islanders. It’s hard out there for a goalie who wants to be No. 1 right now. … The Montreal Canadiens’ top move was to trade for fighter George Parros, which means that the Habs’ biggest addition so far is the ill-conceived signing of Danny Briere. … The Devils, after losing Clarkson, did well to replace him less expensively with Ryane Clowe, but still overpaid, and what Michael Ryder is doing in New Jersey is anyone’s guess. That’s a bizarre fit, and maybe just a hopeful roll of the dice by Lou Lamoriello to add some scoring—at quite a price, though, $7 million over two years.